Although social anxiety disorder (SAD) is most often diagnosed during adolescence, few investigations have examined the clinical presentation and daily functional impairment of this disorder exclusively in adolescents. Prior studies have demonstrated that some clinical features of SAD in adolescents are unique relative to younger children with the condition. Furthermore, quality of sleep, a robust predictor of anxiety problems and daily stress, has not been examined in socially anxious adolescents. In this investigation, social behavior and sleep were closely examined in adolescents with SAD (n = 16) and normal control adolescents (NC; n = 14). Participants completed a self-report measure and an actigraphy assessment of sleep. Social functioning was assessed via a brief speech and a social interaction task, during which heart rate and skin conductance were measured. Additionally, participants completed a daily social activity journal for 1 week. No differences were observed in objective or subjective quality of sleep. Adolescents with SAD reported greater distress during the analogue social tasks relative to NC adolescents. During the speech task, adolescents with SAD exhibited a trend toward greater speech latency and spoke significantly less than NC adolescents. Additionally, SAD participants manifested greater skin conductance during the speech task. During the social interaction, adolescents with SAD required significantly more confederate prompts to stimulate interaction. Finally, adolescents with SAD reported more frequent anxiety-provoking situations in their daily lives, including answering questions in class, assertive communication, and interacting with a group. The findings suggest that, although adolescents with SAD may not exhibit daily impaired sleep, the group does experience specific behavioral and physiological difficulties in social contexts regularly. Social skills training may be a critical component in therapeutic approaches for this group.